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RESEARCH ARTICLE
Contents Vol 69(1)

A New Protocol for Total Synthesis of Natural Product Frutinone A and Its Derivatives

Kang Lei A B , Dong-Wei Sun A B , Yuan-Yuan Tao A B and Xiao-Hua Xu A B C
+ Author Affiliations
- Author Affiliations

A State Key Laboratory of Elemento-Organic Chemistry, Nankai University, Number 94, Weijin Road, Nankai District, Tianjin 300071, China.

B Collaborative Innovation Center of Chemical Science and Engineering (Tianjin), Tianjin 300071, China.

C Corresponding author. Email: xiaohuaxu@nankai.edu.cn

Australian Journal of Chemistry 69(1) 98-106 https://doi.org/10.1071/CH15267
Submitted: 12 May 2015  Accepted: 16 June 2015   Published: 17 July 2015

Abstract

A new protocol for total synthesis of natural product frutinone A was accomplished in three steps by using inexpensive 2′-hydroxyacetophenone as starting material. The key intermediate 3-(2-chlorobenzoyl)-4-hydroxycoumarin was synthesized in one pot through Baker–Venkataraman rearrangement of 2-acetylphenyl 2-chlorobenzoate followed by introduction of methyl chloroformate under basic conditions. Then, base-promoted intramolecular nucleophilic substitution reaction of 3-(2-chlorobenzoyl)-4-hydroxycoumarin provided frutinone A in excellent yield. The synthetic route features good yield, transition metal-free and mild reaction conditions, and high tolerance for functionality, thereby allowing easy substitutions around the frutinone A core.


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